Dispersant compositions and toxicant concentrates containing the same



United States Patent Ofiice 2,976,208 Patented Mar. 21, 1961 DISPERSANTCOMPOSITIONS AND TOXICANT CON CENTRATES CONTAINING THE SAME Paul L.Lindner, Evanston, 11]., assiguor, by mesne assignments, to WitcoChemical Company, Inc., New York, N.Y., a corporation of Delaware NDrawing. Original application Aug. 27, 1956, Ser. No. 606,182. Dividedand this application Feb. 3, 1960, Ser. No. 6,349

15 Claims. (Cl. 16742) My invention relates to the production of new anduseful dispersant compositions and to liquid biocidal toxicantcompositions, particularly in the form of toxicant concentrates,containing said dispersants.

-It has been found to be highly desirable, in certain situations, to beable to apply to an earth soil, in which plant or vegetable life isgrown or contemplated to be grown,'both water-soluble fertilizermaterial and also a desired pesticide, to wit, water-insoluble organicsolventsoluble insecticide or soil fumigant, hereafter genericallycalled biocidal toxicant, in the form of a single composition. Effortsto provide such a composition, for instance, in the form of a stable,mobile, pourable or pumpable liquid emulsion, by simple mixing, presentcertain serious problems. The water-soluble fertilizer materialscomprise water-soluble compounds, typical examples of which arepotassium chloride, potassium nitrate, ammonium nitrate, ammoniumsulphate, potassium sulphate, ammonium phosphate, and urea, with orwithout supplemental materials.

When dissolved in water to form strong solutions, particularly solutionsapproximating concentrated solutions, constituting the aqueous phase,and admixed with biocidal toxicant concentrates containing biocidaltoxicants dis-' solved in organic solvents and insoluble in said aqueousphase, or solutions of such biocidal toxicants in organic solventswherein said latter solutions,.constituting the oleaginous phase, areinsoluble in said aqueous phase, unstable dispersions form which readilyand promptly separate out in the form of layers. Efforts to emulsifysuch aqueous phases and such oleaginous phases .by means of usual typesof emulsifying agents used in the toxicant emulsion field have provedentirely unsatisfactory. Non-ionic emulsifiers of the type of thepolyoxyethylene derivatives of lipophillic materials, for instance,polyethylene glycol ethers of sorbitan monosterate, polyethylene glycolethers of sorbitan monooleate, alkyl phenoxy polyoxyethanols, iso-octylphenol polyoxyethylene ethers, and the like, have been found to beineffective since they are salted out by the strong electrolytes in thehigh concentrations used in liquid fertilizer solutions. Similarly,higher alkyl aryl sulfonates, such as alkali metal, ammonium, magnesiumor calcium salts of dodecyl benzene sulfonate, and the like, havelikewise been found to be entirely unsatisfactory, whether used inconjunction with the non-ionic emulsifiers of the type mentioned aboveor by themselves.

The problem of providing satisfactory emulsions of aqueous liquidfertilizer solutions, particularly strong solutions, containing upwardsof 20% of water-soluble fertilizer ingredients such as the monovalentand polyvalent ionic compounds described above and up to saturatedaqueous solutions of said fertilizer solutions, with water-insolubleorganic solvent-soluble biocidal toxicants has, so far as I am aware,not remotely been solved despite intensive efforts to do so. In certaininstances, by means of special combinations of ingredients,

it has been possible to prepare liquid fertilizer-biocidal toxicantcompositions, but these must be prepared immediately prior to being usedand must be used promptly since, among other things, their stability isof extremely short duration. Other special combinations of ingredientshave been suggested, for instance, which are of use in'liquidfertilizer-biocidal toxicant compositions but only if the liquidfertilizer contains trivalent phosphate ions and urea. In the presenceof monovalent ions such as chlorides or nitrates, such lattercompositions are of no commercial value because the emulsifying actionof the combination of ingredients is destroyed.

I have discovered new and useful biocidal toxicant concentrates (anddispersant compositions for use therein) which, when admixed, by simplemixing, with liquid fertilizer compositions in the form of strongaqueous solutions, say in excess of 20% concentration up to saturation,produce homogeneous emulsions or dispersions which remain usable forperiods. of the order of at least several hours. My invention makes itunnecessary to pre-mix the biocidal toxicant concentrate with Water justprior to admixing it with the liquid fertilizer solution, as is requiredwith certain heretofore known biocidal toxicant concentrates. All thatis necessary, in the case of biocidal toxicant concentrates made inaccord ance with my invention, is simple mixing or agitation with theliquid fertilzer solution. Moreover, my novel biocidal toxicantconcentrates can effectively be used with liquid fertilizer compositionsirrespective of whether the latter contain monovalent or polyvalentions, and they are also usable with more dilute solutions of liquidfertilizers as, for instance, those containing of the order of 10 to 15%of solids. Thus, they have a universality of utility which is a mostimportant practical consideration.

I have discovered that if there are utilized, in admixture, certainmaterials falling into two separate classes, and which are employed incertain ratios with respect to each other, all as is hereafterdescribedin detail, a synergistic effect is obtained which brings about theentirely unpredictable and unexpected results which are achieved by mypresent invention. a

The first of these ingredients, which, for convenience, may be calledthe (a) ingredient, comprises a compound which is a specific type ofderivative of an alcohol amine and which may be characterized as ahigher molecular weight fatty acid ester of an alcohol non-tertiary(that is, primary or secondary) amine, a reactive hydrogen of the amineradical of said alcohol non-tertiary amine being replaced by an acylradical of a sulfopolycarboxylic acid, for instance, the sulfosuccinicacid radical -0C-CHCHa-COOM SOaM wherein M is an alkali metal or anorganic substituted ammonium radical, and M' is an. organic substitutedammonium radical. At least most of said compounds constituting said (a)ingredient may be represented by the formula Ro0o-XNHo0--Y(-o00M)n SOsMwhere RCO- is ,a fatty acyl radical containing atleast 8 and especiallyfrom 12. to 18 carbon atoms, X I

derived from oils or fats, hydrogenated or not, such as coconut oil,babassu oil, corn oil, castor oil, linseed oil, fish oils, cottonseedoil, soya bean oil, palm nut kernel oil, and the like, or fatty acidssuch as lauric acid, myristic acid, palmitic acid, stearic acid, oleicacid, linoleic acid and commercial mixtures of such fatty acidspredonnnant in content of a desired one or ones of said fatty acid, oracylating derivatives of such acids as, for example, the acyl chloridesthereof.

The alcohol primary and secondary amines, particularly water-solublehydroxy-alkyl primary amines, which are utilized to form the higherfatty acid ester linkage in the molecule in the preparation of the (a)ingredient can be selected from a large group, typical or illustrativeexamples of which are monoethanolamine, monopropanolamine,diethanolamine, isopropanolamine, monobutanolamine, isobutanolamine;l-amino-2,3-propanediol; 2-an1ino-l,3-propanediol; diglycerolamine;2-amino-2- methyl-1,3-propanediol; 2amino-2-n-propyl-l,3-propanediol;and 2-amino-2-isopropyl-1,3-propanediol. Of especial utility are, asindicated above, monoethanolaminc and monoisopropanolamine.

The polycarboxylic acids, the sulfo-derivatives of which are employed inthe preparation of the (a) ingredient, can be chosen from a large group,typical or illustrative examples of which are maleic acid, fumaric acid,tartaric acid, glutaconic acid, itaconic acid, adipic acid, phthalicacid, sebacic acid, tricarballylic acid, and glutaric acid. Ofparticular utility are the aliphatic sulfopolycarboxylic acids,especially the water-soluble sulfodicarboxylic acids containing from 4to 8 carbon atoms. The sulfosuccinic acid derivatives are particularlypreferred.

The salt-forming radicals represented by M or M comprise, in the case ofM, alkali metals (which term is here used to mean sodium, potassium,lithium and ammonium); and, in the case of M and M, organic substitutedammonium radicals. The latter, which most advantageously arewater-soluble lower molecular weight amines, may be selected from a widegroup, typical examples of which are dimethylamine; diethylamine;triethylamine; propylamine; monoisopropylamine, diisopropylamine,triisopropylamine, and commercial mixtures of said isopropylamines;butyl amine; amyl amine; monoisopropasubstituted ammonium radical is analkyl amine containing from 1 to 6 carbon atoms, especiallyisopropylamine. In the case of the sulfotricarboxylic acid derivatives,the said salt may be the organic substituted ammonium trisalt, that is,where both M and M are organic substituted ammonium radicals, which maybe the same or diiferent organic substituted ammonium radicals; or thesaid salt may be a one-third alkali metal and two-thirds organicsubstituted ammonium salt, in which case M is an organic substitutedammonium radical and M is an alkali metal; or vice verse, that is, saidsalt may be a two-thirds alkali metal and one-third organic substitutedammonium salt, in which case M is an alkali metal and M is an organicsubstituted ammonium radical.

Illustrative examples of said (a) ingredient are the following (whichinclude, also, the isomers thereof):

Half ammonium half isopropylamine salt of the sultosuc cinic acid amideof the oleic acid ester of isopropanolamine Isopropylamine (ii-salt ofthe sulfosuccinic acid amide of the oleic acid ester of isopropunolamineHalt sodium half butyl amine salt of the suifosuccinic acid amide of thelauric acid ester of isopropanolamine Half ammonium half isopropylaminesalt of the sulfosuccinic acid amide of the palmitic acid ester ofmonoethanolamine H3 CnHarC O O-CH-CHrNH-O C-CH-CHr-COOILHzN-CiI=iC-IIs)| SOsNa Half sodium half isopropylamine salt of thesulfosuccinic acid amide of the oleic acid ester of isopropanoluminenolamine, diisopropanolamine, triisopropanolamine and commercialmixtures of said isopropanolamines; ethanolamines such asmonoethanolamine, diethanolamine, triethanolamine, and commercialmixtures thereof; polyamines such as aminoethyl ethanolamine,ethylenediamine, diethylenetriamine, hydroxyethyl cthylenediamine, andhexamethylenediamine; hexylamine; cyclohexylamine; dimethylbenzylamine,benzylarnine; morpholine; methylcyclohexylamine; alkyl alkanolaminessuch as ethyl diethanolamine and diethyl ethanolamine; furfuryiamine;piperidine; 2-amino-2-methyl-lpropanol; Z-aminol-butanol; methylpiperidine, and the like, and compatible mixtures of any two or morethereof.

In the case of said first or (a) ingredient, it will be seen that, inthe case of sulfodicarboxylic acid derivatives, the said salt may be theorganic substituted ammonium di-salt, that is, where both M and M areorganic substituted ammonium radicals, which may be the same ordifferent organic substituted ammonium radicals; or the said salt may bea half alkalimetal and half organic substituted ammonium salt which isthe case Where M is an alkali metal and M is an organic substitutedammonium radical. Of particular utility, as the first ingredient, arethe organic substituted ammonium di-salts and the half ammonium halforganic substituted ammonium salt of the sulfosuccinic acid amide of theoleic acid ester of isopropanolamine, wherein the organic Half ammoniumhalf cyclohexylamine salt of the sulfosucciuic acid amide of themyristic acid ester of isopropanolamine Half lithium half isopropyiaminesalt of the sulfosuccinic acid amide of the oleic acid ester ofmonoethanolnmine Isopropylamine tri-salt of the sulfotricarballyiie acidamide of the oleic acid ester of monoethanolamine The (a) ingredient,for instance, the half alkali metal half organic substituted ammoniumsalts of the sulfosuccinic acid amides of the higher fatty acid estersof monoethanolamine or isopropanolamine, can readily be made by reactingthe higher fatty acid ester of monoethanoiamine or isopropanolamine withmaleic anhydride and heating to about 100 degrees C. to produce themaleic amide. The free carboxyl group of the maleic acid radical ofamide is then neutralized with an alkali metal or organic substitutedammonium base, and then the resulting compound is reacted with an alkalimetal or amine bisulfite, as the case may be, in an aqueous or aqueousalcohol medium at 60 to degrees C. The desired final product may beremoved and purified for use in the practice of my present inventionalthough purification steps usually will not be necessary. The watercontent of said product, as used in the practice of my invention, shouldnot exceed about 25% and, more advantageously, should be about 15% orless. It will be most convenient to introduce the sulfonic group intothe molecule by the use of 'an alkali metal bisulfite, in which case theprior neutralization of the free carboxyl group of the maleic acidradical of the maleic amide will first have been carried out with theorganic substituted ammonium base if a half alkali metal half organicsubstituted ammonium salt is to 'be prepared. It is not material to thesuccess of my invention which of the M or the M cation is organicsubstituted ammonium radical but, as stated above, one of them should bean alkali metaland the other should be an organic substituted ammoniumradical, or, in the broader aspect of my invention as I have shown, bothM and M' can be an organic substituted ammonium cation. An alternativeprocedure involves neutralizing an alkali metal bisulfite with anorganic substituted ammoniumbase and then utilizing the resulting amineneutralized alkali metal bisulfite in the reaction with the maleic acidamide of the higher fatty acid ester of the monoethanolamine orisopropanolamine. In the formulae given above and in the claims for the(a) ingredient, it will be understood that the M and M may beinterchanged, that is, the M cation may be attached to the S0 radicaland the M cation may be attached to the free carboxyl group of themaleic acid radical, and the claims should be so read. It will beunderstood that the method of making the aforementioned salts of thesulfosuccinic acid amides of the higher fatty acid esters ofmonoethanolamine and isopropanolamine, 'as the case may be, form no partof the present invention and various methods for the production of saidcompounds will readily suggest themselves to those skilled in the art.

The second of said ingredients, which may, for convenience, be calledthe (b) ingredient, is an amine salt of an alkyl benzene sulfonic acidin which the alkyl radical contains from 12 to 18 carbon atoms. Thealkyl radical, which is advantageously predominately a single higheralkyl radical, may be derived from polypropylenes, kerosene fractions,or the like, contains predominately from 12 to 18 carbon atoms, and,especially, predominately from 12 to 15 carbon atoms. The benzenenucleus may also contain lower alkyl substituents, provided that thenumber of carbon atoms in such lower alkyl constituents is in the rangeof from 1 to 3 and the number of such lower alkyl substituents does notexceed 2. The number of sulfonic acid radicals in the benzene nucleusmay be 1 or 2, but, especially, there is only approximately one sulfonicacid radical in the benzene nucleus.

Certain of the higher alkyl benzene sulfonic acids which, in the form oftheir organic amine salts, are employed as the (b) ingredient in thepractice of my invention can be represented by the formula (Rin SOsXwhere R is a lower alkyl radical containing from 1 to 3 carbon atoms,such as methyl, ethyl, propyl and iso-' propyl, R is a higher alkylradical containing from 12 to 18 carbon atoms and especially from 12 to15 carbon atoms, n is zero to 2, and X is'an organic amine cation.

Typical examples of the organic amines whose salts of the higher alkylbenzene sul-fonic acids are employed as the (b) ingredient in accordancewith my present invention are those which have been mentioned above asbeing representative of M in the general formula for the (a) ingredient.Particularly preferred are the alkyl amines containing from 1 to 6carbon atoms and especial- 1y preferred is isopropyl amine. Typical orillustrative examples of the organic amine salts of the higher alkylbenzene sulfonic acids the use of which is encompassed by my inventionare the following: diisopropanolamine zene mono-sulfonic acid; andtriisopropylamine salt of octadecyl benzene di-sulfonic acid; andmixtures of two or more thereof. The isopropylamine salt of dodecylbenzene mono-sulfonic acid is unusually satisfactory as the (b)ingredient and its use, in the combinations here involved, represents animportant, though limited, embodiment of my invention.

It will be understood, of course, that mixtures of any two or more ofthe (a) and any two or more of the (b) ingredients can be employed inthe practice of my present invention.

The biocidal toxicants which are used in accordance with my presentinvention and which, as stated above, comprise insecticides and soilfumigants, may be selected from a Wide group typical examples of whichare Aldrin (1,2,3,4,10,10 hexachloro 1,4,4a,5,8,8ahexahydro-1,4,5,8-dimethanonaphthalene) Dieldrin (1,2,3, 4,10,10hexachloro 6,7 epoxy,1,4,4a,5,6,7,8,8a octahydroxy 1,4 endo exo 5,8dimethanonaphthalene); Lindane (gamma isomer of benzene hexachloride);Heptachlor l,4,5,6,7,8,8 heptachl0ro-3a,4,7,7a-tetrahydro 4,7 endomethanoindene); Nemagon (1,2-dibromo-S-chloropropane); ethylenedibromide; DDT; organic thiocyanates such as B-butoxy,'-thiocyanodiethyl ether, bornyl thiocyanoacetate;trichlorobenzene;propyl, butyl, and amyl ethers of pentachlorophenol,and the like, and compatible mixtures of any two or more thereof. Ofespecial importance are Aldrin, Dieldrin, Lindane, Heptachlor, andNemagon.

The organic solvent which is utilized in the preparation of the biocidaltoxicant concentrates of my present invention, and in which thebiocidaltoxicant is soluble, may be selected from a known group of such organicsolvents. Such organic solvents are of the type which are insoluble inthe aqueous phase and, at least inmost cases, will be per se insolublein water. For convenience, said organic solvents are referred to hereinas being water-insoluble, and the same is true of the biocidaltoxicants, although the criterion is essential insolubility in theaqueous phase of the emulsion. These include, for instance, aromatichydrocarbon solvents, or blends thereof with paraflinic or naphthenicsolvents. Examples of such solvents are kerosene; light refined mineraloil; methylnaphthalenes such' as monomethyl naphthalene, dimethylnaphthalene and trimethyl naphthalene; ethyl naphthalene;2-methylpentanediol-1,2; dip-ropyleneglycol methyl ethers; benzene,toluene, aromatic naphthas, xylene, tetrahydronaphthalene, cyclohexane,and the like. These and various other organic solvents are frequentlysold under trade names, such as Cyclosol 53, which is an aromaticpetroleum friction comprising methylated naphthalenes; and Sovacide 544Cwhich is an aromatic I ingredients, by weight of the biocidal toxicantconcentrate, will fall within the range of 3 to 30%,- but, 'ordi narily,from 6 to 15 and, particularly, from 8 to 12%,

will be found quite satisfactory for most purposes. The relativeproportions of the (a) and (b) ingredients, or, in other words, theweight ratio of the (a) to the (b) ingredient, should be at least 2 tol, and is usually in the range of about 2 to about 20, preferably on anaverage of about 4 to 10, parts of the (a) ingredient to 1 part of the(b) ingredient. The upper limit of the (a) ingredient may, if desired,be at least several times the values recited above. Within the limitsstated, the proportions of ingredients may be varied in order to obtainoptimum results in connection with any particular liquid fertilizersolution.

The liquid fertilizer solutions (with which the hereinabove describedbiocidal toxicant concentrates are admixed to form homogeneous emulsionsor dispersions which are usable over periods of at least several hours)are, per se, Well known in the art. They comprise aqueous solutions,usually strong or concentrated aqueous solutions even up to saturation,of water-soluble compounds which fall into the category of providing atleast one of the elements potassium, nitrogen and phosphorus, including,among others, as previously pointed out, potassium chloride, potassiumnitrate, potassium sulphate, ammonium nitrate, ammonium sulphate,ammonium phosphate, aqueous ammonia, and the like, as well as organicwater-soluble fertilizer materials particularly in conjunction with theinorganic water-soluble salts, such as those mentioned above, anespecially preferred example of such organic water-soluble fertilizermaterial being urea. The liquid fertilizers, which will normally includeone or more of the aforementioned materials, may be standardized as totheir nitrogen, phosphorus (as P and potassium (as K 0) contents.Typical examples of liquid fertilizer solutions, which can be used inconjunction with the novel biocidal toxicant concentrates of myinvention are shown in a bulletin entitled Preparation of LiquidFertilizers, Second Edition, published by Victor Chemical Works,Chicago, Illinois.

The following examples are illustrative of biocidal toxicantconcentrates, and dispersant compositions for use therein, fallingwithin the scope of my invention. Other specific embodiments willreadily occur to those skilled in the art in the light of the guidingteachings and principles disclosed herein. All parts listed are byweight.

Example A Parts Aldrin (90%) 27.6 Kerosene (deodorized) 32 Cyclosol 53(organic solvent) 30.4

Half ammonium half isopropylamine salt of the sulfosuccinic acid amideof the oleic acid ester of isopropanolamine 8 Isopropylamine salt ofdodecyl benzene sulfonic acid 8 Example D Parts Half ammonium halfisopropylamine salt of the sulfosuccinic acid amide of the oleic acidester of isopropanolamine 4 Isopropylamine salt of dodecyl benzenesulfonic acid Example E Parts Isopropylamine di-salt of thesulfosuccinic acid amide of the palmitic acid ester of monoethanolamine5 Isopropylamine salt of dodecyl benzene sulfonic acid l Kerosene 1.5Cyclosol 53 (organic solvent) 15 In the use of the biocidal toxicantconcentrates of my present invention, it will be understood, of course,that the amount of the liquid fertilizer solution will be many times theamount of the biocidal toxicant concentrate. In other words, the aqueousphase of the emulsion will, in all cases, be present in large excessover the olcaginous phase present in the biocidal toxicant concentrate.While such excess may vary somewhat, in the usual case it will be in therange of about 25 or 30 to 60 or even more times that of the oleaginousphase, but will usually be from about 30 to 40 times that of theoleaginous phase, all in terms of parts by weight.

In the use of the biocidal toxicant concentrates of my invention, thesame are simply admixed with the aqueous or liquid fertilizer solution,with suitable agitation. For instance, 2.5 parts of the toxicantconcentrate of Example A are admixed, with stirring, with 97.5 parts ofa liquid fertilizer solution made up of 40 parts of 24.3% aqueousammonia, 45.87 parts of 75% phosphoric acid, and 14.13 parts of Water,all of said parts being by weight. In another typical example, 3 partsof the toxicant concentrate of Example B are admixed with 97 parts ofsaid liquid fertilizer solution. Again, 3.3 parts of the toxicantconcentrate of Example C are admixed with 96.7 parts of a liquidfertilizer solution made up of 44.3 parts ammonium nitrate, 35.4 partsurea, and 20.3 parts of water. Other illustrative commercial types ofliquid fertilizer solutions with which my novel biocidal toxicantconcentrates can be used are the so-called 8-25-0 (derived from ammoniumphosphate); 8-8-8 (derived from ammonium phosphate, potassium chlorideand urea); Uran 32 (derived from ammonium nitrate and urea), and l0-20-0(derived from ammonium phosphate and urea).

This application is a division of my prior application Serial No.606,182, filed August 27, 1956.

What I claim as new and desire to protect by Letters Patent of theUnited States is:

l. A dispersant composition, soluble in organic solvent solutions ofwater-insoluble biocidal toxicants, comprising (a) a compound in theform of a higher fatty acid ester of an alcohol non-tertiary amine, thehigher fatty acid acyl radical of said ester containing from 8 to 18carbon atoms, and a reactive hydrogen of the amine radical of saidnon-tertiary amine being replaced by an acyl radical of asulfopolycarboxylic acid, said latter acyl radical containing from 4 to8 carbon atoms and being represented by the formula wherein Y is thecompletely decarboxylated residue of said polycarboxylic acid, M is amember of the group consisting of alkali metals and organic substitutedammonium radicals, M is an organic substituted ammonium radical, and nis an integer from 1 to 2, and (b) an amine salt of an alkyl benzenesulfonic acid in which the alkyl radical contains from 12 to 18 carbonatoms, the weight ratio of said (a) to said (b) ingredient being atleast 2 to 1.

2. A dispersant composition, soluble in organic solvent solutions ofwater-insoluble biocidal toxicants, comprising (a) a compoundcorresponding to the formula wherein RCO is a fatty acid acyl radicalcontaining from 12 to 18 carbon atoms, X is the completely de aminatedand dehydroxylated residue, of water-soluble alcohol non-tertiary amine,Y is the completely decarboxylated residue of a water-solublepolycarboxylic acid containing from 4 to 8 carbon atoms, M is a memberselected from the group consisting of alkali metals and lower organicsubstituted ammonium radicals, M is a lower organic substituted ammoniumradical, and n is an integer from 1 to 2, and (b) an amine salt of analkyl benzene sulfonic acid in which the alkyl radical contains from 12to 18 carbon atoms, the Weight ratio of said (a) to said (b) ingredientbeing at least 2 to 1.

3. A dispersant composition in accordance with claim 2,-

wherein M and M' are alkyl ammonium containing from 1 to 6 carbon atoms,and the amine salt of the alkyl benzene sulfonic acid is an alkyl aminecontaining from 1 to 6 carbon atoms.

4. A dispersant composition, soluble in organic solvent solutions oforganic water-insoluble biocidal toxicants, comprising (a) a compoundcorresponding to the formula wherein R-CO is a fatty acid acyl radicalcontaining from 12 to 18 carbon atoms, X is the completely deaminatedand dehydroxylated residue of a hydroxyalkyl primary amine selected fromthe group consisting of monoethanolamine and monoisopropanolamine, M isa member selected from the group consisting of alkali metals and organicsubstituted ammonium radicals, and M is alkyl ammonium, and (b) an alkylamine salt of an alkyl benzene sulfonic acid corresponding to theformula where R is a lower alkyl radical containing from 1 to 3 carbonatoms, R is a higher alkyl radical containing from 12 to 18 carbonatoms, n is zero to 2, and X is an organic amine cation, the weightratio of said (a) to said (b) ingredient being at least 2 to l.

5. A dispersant composition, soluble in organic solvent solutions oforganic water-insoluble biocidal toxicants, comprising (a) an organicsubstituted ammonium di-salt of the sulfosuccinic acid amide of a fattyacid ester of monoisopropanolamine the fatty acid radical of whichcontains from 12 to 18 carbon atoms, and (b) an amine salt of dodecylbenzene sulfonic acid, the weight ratio of said (a) to said (b)ingredient being at least 2 to 1.

6. A dispersant composition, soluble in organic solvent solutions oforganic water-insoluble biocidal toxicants, comprising (a) a compoundcorresponding to the formula where M and M are dissimilar and areselected from the group consisting of alkali metals and organicsubstituted ammonium radicals, and (b) an alkyl amine salt of dodecylbenzene sulfonic acid, the alkyl amine radical containing from 1 to 6carbon atoms, the weight ratio of said (a) to said (b) ingredient beingfrom about 2 to about 6 of (a) to 1 of (b).

7. A dispersant composition, soluble in organic solvent 10 solutions oforganic water-insoluble biocidal toxicants, comprising (a) a compoundcorresponding to the formula CH: R-oo-o- 'JH-oH,-NH-0 CCH-OHCOOM sonrM'where R-CO is a fatty acid acyl radical containing from 12 to 18 carbonatoms, and M and M are dissimilar and are selected from the groupconsisting of alkalimetals and isopropyl ammonium, and (b) the isopropylamine salt of dodecyl benzene sulfonic acid, the weight ratio of said(a) to said (b) ingredient being from about 2 to 6 of (a) to 1 of (b).

8. A toxicant concentrate comprising an organic solvent solution of anorganic water-insoluble biocidal toXicant and containing, dissolvedtherein, (a) a compound in the form of a higher fatty acid ester of analcohol non-tertiary amine, the higher fatty acid acyl radical of saidester wherein Y is the completely decarboxylated residue of saidpolycarboxylic acid, M is a member of the group consisting .of alkalimetals and organic substituted ammonium radicals, M is an organicsubstituted ammonium radical, and n is an integer from 1 to 2, and (b)an amine salt of an alkyl benzene sulfonic acid in which the alkylradical contains from 12 to 18 carbon atoms, the weight ratio of said(a) to said (b) ingredient being at least 2 to l, the total of said (a)and (b) ingredients constituting from 3 to 30%, by weight, of saidconcentrate, said concentrate being adapted, upon admixture with aqueoussolutions containing upwards of 20% of fertilizer ingredients, to form ahomogeneous dispersion usable for periods of the order of at leastseveral hours.

9. A toxicant concentrate comprising an organic solvent solution of anorganic Water-insoluble biocidal toxicant and containing, dissolvedtherein, (a) a compound corresponding to the formula 7 wherein R-CO- isa fatty acid acyl' radical containing from 12 to 18 carbon atoms, X isthe completely dea'minated and dehydroxylated residue of a Water-solublealcohol non-tertiary amine, Y is the completely decarboxylated residueof a water-soluble polycarboxylic acid containing from 4 to 8 carbonatoms, M is a member selected from the group consisting of alkalimetalsand lower organic substituted ammonium radicals, M is a lowerorganic substituted ammonium radical, and n is an integer from 1 to 2,and (b) an amine salt of an alkyl benzene sulfonic acid in which thealkyl radical contains from 12 to 18 carbon atoms, the weight rati'ofofsaid (a) to said (b) ingredient being at least 2 to 1'.

10. A toxicant concentrate in accordance with claim 13, wherein M and Mare alkyl ammonium containing RCOOXNH-O COHCE;-COOM wherein R-CO is afatty acid acyl radical containing 1 1 from 12 to 18 carbon atoms, X isthe completely deaminated and dehydroxylated residue of a hydroxyalkylprimary amine selected from the group consisting of monoethanolamine andmonoisopropanolamine, M is a member selected from the group consistingof alkali metals and organic substituted ammonium radicals, and M isalkyl ammonium, and (b) an alkyl amine salt of an alkyl benzene sulfonicacid corresponding to the formula where R is a lower alkyl radicalcontaining from 1 to 3 carbon atoms, R is a higher alkyl radicalcontaining from 12 to 18 carbon atoms, 11 is zero to 2, and X is anorganic amine cation, the weight ratio of said (a) to said (b)ingredient being at least 2 to 1, the total of said (a) and (b)ingredients constituting from 3 to 30%, by weight, of said concentrate,said concentrate being adapted, upon admixture with aqueous solutionscontaining upwards of 20% of fertilizer ingredients, to form ahomogeneous dispersion usable for periods of the order of at leastseveral hours.

12. A toxicant concentrate comprising an organic solvent solution of anorganic water-insoluble biocidal toxicant and containing, dissolvedtherein, (a) a compound corresponding to the formula where M and M aredissimilar and are selected from the, group consisting of alkali metalsand organic substituted ammonium radicals, and (b) an alkyl amine saltof dodecyl benzene sulfonic acid, the alkyl amine radicals containingfrom 1 to 6 carbon atoms, the Weight ratio of said (a) to said (b)ingredient being from about 2 to about 20 of (a) to 1 of (b), the totalof said (a) and (b) ingredients constituting from 6 to 15%, by weight,of said concentrate, said concentrate being adapted, upon admixture withaqueous solutions containing upwards of 20% of fertilizer ingredients,to form a homogeneous dispersion usable for periods of the order of atleast several hours.

13. A toxicant concentrate comprising an organic solvent solution of anorganic water-insoluble biocidal toxicant and containing, dissolvedtherein, (a) a compound corresponding to the formula lCH? 11-0o-o-Cn-cm-un-o CCHCHa-C o OM SOsELM where R-CO is a fatty acid acylradical containing from 12 to 18 carbon atoms, and M and M aredissimilar and are selected from the group consisting of alkali metalsand isopropyl ammonium, and (b) an alkylamine salt of dodecyl benzenesulfonic acid, the weight ratio of said (a) to said (b) ingredient beingfrom about 2 to 20 of (a) to 1 of (b), the total of said (a) and (b)ingredients constituting from 6 to 15%, by weight, of said concentrate,said concentrate being adapted, upon admixture with aqueous solutionscontaining upwards of 20% of fertilizer ingredients, to form ahomogeneous dispersion usable for periods of the order of at leastseveral hours.

14. A combination biocidal toxicant water-soluble inorganic saltfertilizer composition containing an aqueous phase comprising a watersolution of said water-soluble inorganic salt fertilizer material, and anormally waterimmiscible oleaginous phase comprising an organic solventsolution of said biocidal toxicant, said composition comprising asubstantially homogeneous emulsion which includes, in admixturetherewith, (a) a compound in the form of a higher fatty acid ester of analcohol nontertiary amine, the higher fatty acid acyl radical of saidester containing from 8 to 18 carbon atoms, and a reactive hydrogen ofthe amine radical of said non-tertiary amine being replaced by an acylradical of a sulfopolycarboxylic acid, said latter acyl radicalcontaining from 4 to 8 carbon atoms and being represented by the formula soot wherein Y is the completely decarboxylated residue of saidpolycarboxylic acid, M is a member of the group consisting of alkalimetals and organic substituted ammonium radicals, M is an organicsubstituted ammonium radical, and n is an integer from 1 to 2, and (b)an amine salt of an alkyl benzene sulfonic acid in which the alkylradical contains from 12 to 18 carbon atoms, the weight ratio of said(a) to said (b) ingredient being at least 2 to 1, the total of said (a)and (b) ingredients constituting from 3 to 30%, by weight, of thewaterimmiscible oleaginous phase.

15. A combination biocidal toxicant water-soluble inorganic saltfertilizer composition containing an aqueous phase comprising a watersolution of at least 20% of said water-soluble inorganic salt fertilizermaterial, and a normally water-immiscible oleaginous phase comprising anorganic solvent solution of said biocidal toxicant, said compositioncomprising a substantially homogeneous emulsion which includes, inadmixture therewith, (a) a compound corresponding to the formula whereinM and M are dissimilar and are selected from the group consisting ofalkali metals and organic substituted ammonium radicals, and (b) theisopropyl amine salt of dodecyl benzene sulfonic acid, the weight ratioof said (a) to said (b) ingredient being from about 2 to about 20 of (a)to 1 of (b), the total of said (a) and (b) ingredients constituting from6 to 15%, by weight, of the water-immiscible oleaginous phase.

References Cited in the file of this patent UNITED STATES PATENTS2,236,528 Epstein et a1 Apr. 1, 1941 2,236,529 Epstein et al Apr. 1,1941 2,686,201 Keenan Aug. 10, 1954 2,731,338 Fike Jan. 17, 19562,756,135 Searle July 24, 1956 OTHER REFERENCES Brown et a1.: Soap,Formulations of Emulsions," July 1951, pp. 43, 45, 47 and 49.

1. A DISPERSANT COMPOSITION, SOLUBLE IN ORGANIC SOLVENT SOLUTIONS OFWATER-INSOLUBLE BIOCIDAL TOXICANTS, COMPRISING (A) A COMPOUND IN THEFORM OF A HIGHER FATTY ACID ESTER OF AN ALCOHOL NON-TERTIARY AMINE, THEHIGHER FATTY ACID ACYL RADICAL OF SAID ESTER CONTAINING FROM 8 TO 18CARBON ATOMS, AND A REACTIVE HYDROGEN OF THE AMINE RADICAL OF SAIDNON-TERTIARY AMINE BEING REPLACED BY AN ACYL RADICAL OF ASULFOPOLYCARBOXYLIC ACID, SAID LATTER ACYL RADICAL CONTAINING FROM 4 TO8 CARBON ATOMS AND BEING REPRESENTED BY THE FORMULA